EP0600322B1 - Schwarze Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial - Google Patents

Schwarze Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial Download PDF

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Publication number
EP0600322B1
EP0600322B1 EP93118647A EP93118647A EP0600322B1 EP 0600322 B1 EP0600322 B1 EP 0600322B1 EP 93118647 A EP93118647 A EP 93118647A EP 93118647 A EP93118647 A EP 93118647A EP 0600322 B1 EP0600322 B1 EP 0600322B1
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EP
European Patent Office
Prior art keywords
dye
dyes
sulfatoethylsulfonyl
formula
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP93118647A
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German (de)
English (en)
French (fr)
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EP0600322A2 (de
EP0600322A3 (de
Inventor
Kurt Dr. Hussong
Werner Hubert Dr. Russ
Karl Krieger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dystar Textilfarben GmbH and Co Deutschland KG
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Dystar Textilfarben GmbH and Co Deutschland KG
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Publication of EP0600322A3 publication Critical patent/EP0600322A3/de
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Publication of EP0600322B1 publication Critical patent/EP0600322B1/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0047—Mixtures of two or more reactive azo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0047—Mixtures of two or more reactive azo dyes
    • C09B67/005—Mixtures of two or more reactive azo dyes all the reactive groups being not directly attached to a heterocyclic system
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/10—Material containing basic nitrogen containing amide groups using reactive dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups

Definitions

  • the invention is in the technical field of fiber-reactive dyes.
  • the fiber-reactive Group is a ⁇ , ⁇ -dichloroethylsulfonyl or ⁇ -chlorovinylsulfonyl group.
  • the Individual dyes of these dye mixtures consist of a navy blue Disazo dye with a 1-amino-8-hydroxy-naphthalene-3,6-disulfonic acid as bivalent coupling component and a 2,5-disulfophenyl radical as one and a phenyl group with said fiber reactive group as the other Diazo component and an orange monoazo dye with the 6,8-disulfo-2-naphthol coupling component and an aniline with said fiber-reactive group as a diazo component.
  • the dyes of the general formulas (1) and (2) are numerous in the literature described. So are the disazo dyes of the general formula (1) for example from U.S. Patent 2,657,205 and from Japanese Patent application publication Sho-58-160 362 and from U.S. Patent 4,257,770 and the literature cited therein. Monoazo dyes of general formula (2) are in the U.S. patent 5,093,483.
  • the dye mixtures from the dyes preferably contain general formulas (1) and (2) to the disazo dyes of the formula (1) 60 to 80 wt .-% and the or the monoazo dyes of the formula (2) to 20 to 40% by weight.
  • a sulfo group is a group of the general formula -SO 3 M
  • a carboxy group is a group of the general formula -COOM
  • a sulfato group is a group of the general formula -OSO 3 M
  • a thiosulfato group is a group of the general formula -S-SO 3 M.
  • the dyes of the formula (1) and also the dyes of the formula (2), especially with the same chromophore, can have different fiber-reactive groups -SO 2 -Y within the meaning of Y.
  • the dye mixtures can contain dyes of the same chromophore according to the general formula (1) and / or dyes of the same chromophore according to the general formula (2) in which the fiber-reactive groups -SO 2 -Y are vinylsulfonyl groups and ⁇ -chloroethylsulfonyl or are ⁇ -thiosulfatoethylsulfonyl or preferably ⁇ -sulfatoethylsulfonyl groups.
  • the dye mixtures contain the respective dye components in the form of a vinylsulfonyl dye
  • the amount of dye in the respective vinylsulfonyl dye for the particular ⁇ -chloro or ⁇ -thiosulfato or ⁇ -sulfatoethylsulfonyl dye is up to about 30 mol%, based on the respective dye chromophore.
  • Dye mixtures in which the proportion of the vinylsulfonyl dyes to the ⁇ -sulfatoethylsulfonyl dyes in Molar ratio is between 5:95 and 30:70.
  • Dye mixtures of one or more disazo dyes corresponding to the general formula (10) and one or more monoazo dyes corresponding to the general formula (11) are also preferred.
  • M has one of the meanings mentioned above and D 1 , D 2 and D 3 each, independently of one another, 3-vinylsulfonylphenyl, 4-vinylsulfonylphenyl, 3- ( ⁇ -sulfatoethylsulfonyl) phenyl or 4- ( ⁇ -sulfatoethylsulfonyl ) -phenyl means, where in the case that both vinylsulfonyl and ⁇ -sulfatoethylsulfonyl groups are present in the dye mixtures, the molar ratio between the vinylsulfonyl components and the ⁇ -sulfatoethylsulfonyl components in a molar ratio between 5:95 and 30:70 lies.
  • dye mixtures of one or more dyes of the general formula (10) and one or more dyes of the general formula (11) are preferred, in which D 1 and D 2 both, independently of one another, 3- ( ⁇ -sulfatoethylsulfonyl) phenyl, Is 4- ( ⁇ -sulfatoethylsulfonyl) phenyl, 3-vinylsulfonylphenyl or 4-vinylsulfonylphenyl and D 3 is 2-methoxy-5- ( ⁇ -sulfatoethylsulfonyl) phenyl or 2-methoxy-5-vinylsulfonylphenyl, in the event that both vinylsulfonyl and ⁇ -sulfatoethylsulfonyl groups are present in the dye mixtures, the molar ratio between the vinylsulfonyl components and the ⁇ -sulfatoethylsulfonyl components is in the molar ratio
  • the dye mixtures according to the invention can be prepared in solid form or in liquid (dissolved) form.
  • solid form they contain in general those with water-soluble and especially fiber-reactive dyes usual electrolyte salts, such as sodium chloride, potassium chloride and sodium sulfate, and can furthermore contain the auxiliaries customary in commercial dyes, such as buffer substances which have a pH in aqueous solution between 3 and 7 able to adjust, such as sodium acetate, sodium borate, Sodium bicarbonate, sodium dihydrogen phosphate and Disodium hydrogen phosphate, small amounts of siccatives or, if in liquid, aqueous solution (including the content of thickeners, as they are common with printing pastes), substances that increase the durability ensure these preparations, such as anti-mold Medium.
  • buffer substances which have a pH in aqueous solution between 3 and 7 able to adjust, such as sodium acetate, sodium borate, Sodium bicarbonate, sodium dihydrogen phosphate and Disodium hydrogen phosphate, small
  • the dye mixtures are in the form of a dye powder Content of 10 to 80 wt .-%, based on the dye powder or Preparation, on an electrolyte salt, which is also referred to as a setting agent, in front.
  • These dye powders can also contain the buffer substances mentioned a total of up to 5%, based on the dye powder.
  • the total dye content in these aqueous solutions is up to about 50% by weight, such as between 5 and 50% by weight the electrolyte salt content in these aqueous solutions is preferably below 10 %
  • the aqueous solutions (Liquid preparations) the buffer substances mentioned can usually be found in an amount of up to 5 wt .-%, preferably up to 2 wt .-%, contain.
  • the dye mixtures according to the invention can be prepared in a customary manner, for example by mechanical mixing of the individual dyes in the required proportions or by synthesis using the customary diazotization and coupling reactions using appropriate mixtures of the diazo and coupling components in a manner familiar to the person skilled in the art and for this purpose required proportions.
  • the second coupling reaction with the monoazo dye formed to the disazo dye takes place with a further diazo component at a pH between 3 and 6. Then, by adding the aqueous solution of the 2-hydroxy-naphthalene-6-carboxylic acid and a further diazo component, the coupling reaction to the monoazo dye is carried out accordingly of the general formula (2) at a pH between 3 and 6.
  • the dye mixture obtained in this way can be isolated from the solution in a customary manner, for example by salting out with an electrolyte salt, such as sodium chloride, potassium chloride or lithium chloride, or by spray drying.
  • Dye mixtures in which the dye chromophores, for example, in addition to a ⁇ -chloroethylsulfonyl or ⁇ -thiosulfatoethylsulfonyl or ⁇ -sulfatoethylsulfonyl group still contain portions with vinylsulfonyl groups can use the appropriate method in addition to the above Vinylsulfonyl starting anilines can also be prepared in such a way that the dye mixture in which Y is for a ⁇ -chloroethyl or ⁇ -thiosulfatoethyl or ⁇ -sulfatoethyl radical, with one only for a part of these groups the required amount of alkali and thereby some of the above ⁇ -substituted ethylsulfonyl groups converted into the vinylsulfonyl groups. This measure takes place according to generally known methods of Conversion of ⁇ -substituted ethylsulfon
  • the dye mixtures according to the invention from the dyes of the formulas (1) and (2) provide numerous after those in the art for fiber-reactive dyes described application and fixing methods on hydroxy and / or fiber materials containing carbonamide groups deep black dyeings with good Color build-up and good washability of unfixed dye components.
  • the dyeings obtained can be easily etched.
  • the present invention therefore also relates to the use of Dye mixtures according to the invention for dyeing (including printing) of fiber materials containing hydroxyl and / or carbonamide groups or Process for dyeing such fiber materials using a dye mixture according to the invention by the dye mixture in dissolved form applied to the substrate and the dyes by action an alkaline agent, or heat, or both fixed on the fiber.
  • Materials containing hydroxyl groups are natural or synthetic materials containing hydroxyl groups, such as cellulose fiber materials, also in the form of paper, or their regenerated products and polyvinyl alcohols.
  • Cellulose fiber materials are preferably cotton, but also others Vegetable fibers such as linen, hemp, jute and ramie fibers; regenerated Cellulose fibers are, for example, cellulose and viscose rayon.
  • Materials containing carbonamide groups are, for example, synthetic and natural polyamides and polyurethanes, especially in the form of fibers, for example wool and other animal hair, silk, leather, polyamide-6,6, Polyamide-6, polyamide-11 and polyamide-4.
  • the dye mixtures according to the invention are used after generally known methods for dyeing and printing fiber materials according to the known application techniques for fiber-reactive dyes.
  • the dyes of the dye mixtures according to the invention to one another show good combination behavior
  • the invention Dye mixtures are also used with advantage in the pull-out dyeing process become. Accordingly, they can be obtained with cellulose fibers, for example after pulling out from a long liquor at temperatures between 40 and 105 ° C, optionally at temperatures up to 130 ° C under pressure, and optionally in the presence of conventional dyeing aids
  • Use of acid-binding agents and optionally neutral salts, such as sodium chloride or sodium sulfate dyeings in very good color yields and with an excellent color structure and the same nuance.
  • the acid-binding and the fixation of the dyes on the cellulose fibers effecting agents are, for example, water-soluble basic salts of Alkali metals and the alkaline earth metals of inorganic or organic Acids, as well as compounds that release alkali in the heat.
  • the alkali metal hydroxides and alkali metal salts of to name weak to moderate inorganic or organic acids, of the alkali compounds preferably the sodium and Potassium compounds are meant.
  • Such acid-binding agents are for example sodium hydroxide, potassium hydroxide, sodium carbonate, Sodium bicarbonate, potassium carbonate, sodium formate, Sodium dihydrogen phosphate and disodium hydrogen phosphate.
  • the dyes of the invention are chemically attached to the cellulose fiber bound; especially the cellulose dyeings show according to the usual Post-treatment by rinsing to remove unfixed ones Dye proportions have excellent wet fastness properties, especially since they did not fix Wash out dye parts easily because of their good cold water solubility to let.
  • the dyeings on polyurethane and polyamide fibers are usually made from acidic environment. So you can, for example, the dyebath acetic acid and / or ammonium sulfate and / or acetic acid and ammonium acetate or Add sodium acetate to get the desired pH.
  • leveling aids such as based on a Reaction product of cyanuric chloride with three times the molar amount of one Aminobenzenesulfonic acid or aminonaphthalenesulfonic acid or based on a Reaction product of, for example, stearylamine with ethylene oxide.
  • the material to be colored is at a temperature of around 40 ° C Bath introduced, moved there for some time, then the dye bath on the desired weakly acidic, preferably weakly acetic acid pH adjusted and the actual coloring at a temperature between 60 and 98 ° C carried out.
  • the dyeings can also at boiling temperature or at temperatures up to 120 ° C (under pressure).
  • Parts by weight are Parts by weight, the percentages are percentages by weight, if not noted otherwise. Parts by weight are in relation to parts by volume Kilograms to liters.
  • an electrolyte salt-containing dye powder which contains the navy-blue disazo dye of the formula (A) contains 50%
  • 75 parts of an electrolyte salt-containing dye powder which contains the gold-yellow coloring monoazo dye of the formula (B) contains 70% mixed in a mechanical mixer.
  • the resulting dye mixture according to the invention gives dyeings and prints in deep black tones, for example on cellulose fiber materials, using the application and fixing processes customary in the art for fiber-reactive dyes.
  • a suspension of 288 parts of 4- ( ⁇ -sulfatoethylsulfonyl) aniline in 250 parts of water with about 59 parts of sodium carbonate is adjusted to a pH of 4.5 to 5, and the aniline compound is diazotized with 143 parts by volume of one 38% aqueous sodium nitrite solution after addition of 234 parts by volume of 30% aqueous hydrochloric acid and 400 parts of ice, then 112 parts of 1-amino-8-naphthol-3,6-disulfonic acid are added and the first coupling reaction is carried out at a pH between 1 and 1.3 and a temperature below 20 ° C by (the pH range is maintained by about 60 parts of sodium bicarbonate).
  • a black dye solution is obtained in which the dyes of the formulas (A) and (B) mentioned in Example 1 are present in a ratio of 68.7% to 31.3%.
  • This dye solution can be adjusted to a pH of 4.5 by adding 5 parts of a sodium phosphate buffer.
  • this liquid dye mixture can then be adjusted to the desired strength for a liquid preparation, which is used in the customary manner either directly, optionally after adding the appropriate amount of an alkaline agent, as a dye bath or liquor the preparation of a dye bath or dye liquor.
  • This dye mixture gives deep black colorations.
  • an analog Dye mixture can be prepared if the starting compounds in the amount used varies, for example, by the 4- ( ⁇ -sulfatoethylsulfonyl) aniline in an amount of 280 parts, the 1-amino-8-naphthol-3,6-disulfonic acid in an amount of 102 parts and the 2-hydroxy-naphthalene-6-carboxylic acid 68 parts.
  • the dye mixture can be isolated from the synthesis solution, for example by spray drying or directly in the dissolved form as a liquid preparation, as in Example 2 described, are used for dyeing. It delivers likewise, for example on cellulose fiber materials, according to those in the art usual application and fixation procedures deep black colorations.
  • the solution of the dye mixture according to the invention prepared in Example 2 is used. 25% by volume of this solution are separated off, adjusted to a pH of 8 with sodium carbonate and the batch is stirred for a further 15 minutes at 20 ° C., the ⁇ -sulfatoethylsulfonyl groups being converted into the vinylsulfonyl groups.
  • a pH of 4.5 is then set using sulfuric acid and this solution of the vinylsulfonyl dye mixture is added to the original solution of the ⁇ -sulfatoethylsulfonyl dye mixture.
  • An aqueous solution of dyes corresponding to the general formulas (A-1) and (B-1) is obtained. in which Y means 25% vinyl and 75% ⁇ -sulfatoethyl.
  • Inorganic salts such as sodium sulfate, which have additionally entered the aqueous dye solutions as a result of this measure, can in some cases be eliminated by cooling the solution to 0 ° C. and filtered off.
  • the filtrate is adjusted to pH with 5 parts of a sodium phosphate buffer set from 4.5.
  • a sodium phosphate buffer set from 4.5.
  • the first coupling reaction leads to a pH value of 1 to 1.3 and at a temperature below 20 ° C and then isolate the Monoazo compound obtained by salting out with sodium chloride.
  • a solution of 261 parts is added in a separate batch 2-methoxy-5- ( ⁇ -sulfatoethylsulfonyl) aniline in 300 parts of water with 190 parts by volume of a 31% aqueous hydrochloric acid and 300 parts of ice and diazotized using 117.5 parts by volume of a 38% strength aqueous solution Sodium nitrite solution. Then add to this diazonium salt solution the monoazo compound obtained above and 79 parts of 2-hydroxy-naphthalene-6-carboxylic acid and performs the coupling reaction while observing a pH between 5 and 6 and at a temperature of around 20 ° C.
  • the solution thus obtained of a dye mixture according to the invention of the dye of the formula (A) and of the dye (C) can be supplied either directly after isolation of the dye mixture from the synthesis solution by spray drying or by salting out with sodium chloride or directly in the dissolved form for use in dyeing in a conventional procedure.
  • Dyeing of a deep black shade is also obtained, for example on cellulose fiber materials by the application and fixing processes customary for fiber-reactive dyes.
  • an electrolyte-containing dye powder which contains 70% of the orange-coloring monoazo dye of the above formula (C), 200 parts of an electrolyte-containing dye powder which contains 50% of the marine blue-coloring disazo dye of the formula (A), and - for the purpose of shading - 20 parts of an electrolyte-containing dye powder which contains the yellow-coloring monoazo dye of the formula (E) contains 50%, are mixed together in a mechanical mixer.
  • the dye mixture according to the invention using the application and fixing methods customary in the prior art for fiber-reactive dyes, gives dyeings and prints in deep black tones, for example on cellulose fiber materials.
  • the procedure for producing a dye mixture according to the invention is as follows the details of Example 2a, but by using the starting compounds replaced by the following starting compounds or quantities: 290 parts of 4- (8-sulfatoethylsulfonyl) aniline, 102 parts of 1-amino-8-naphthol-3,6-disulfonic acid, 64 parts of 2-hydroxy-naphthalene-6-carboxylic acid and 17 parts 1-benzoylamino-8-naphthol-3,6-disulfonic acid.
  • a dye mixture is obtained, the cellulose fiber materials in a deep Black colors.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
EP93118647A 1992-11-28 1993-11-19 Schwarze Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial Expired - Lifetime EP0600322B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE4240069 1992-11-28
DE4240069 1992-11-28
DE4301025 1993-01-16
DE4301025 1993-01-16

Publications (3)

Publication Number Publication Date
EP0600322A2 EP0600322A2 (de) 1994-06-08
EP0600322A3 EP0600322A3 (de) 1995-02-15
EP0600322B1 true EP0600322B1 (de) 2000-03-15

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EP93118647A Expired - Lifetime EP0600322B1 (de) 1992-11-28 1993-11-19 Schwarze Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial

Country Status (10)

Country Link
US (1) US5445654A (enrdf_load_stackoverflow)
EP (1) EP0600322B1 (enrdf_load_stackoverflow)
JP (1) JPH06263997A (enrdf_load_stackoverflow)
KR (1) KR100293392B1 (enrdf_load_stackoverflow)
CN (1) CN1099052A (enrdf_load_stackoverflow)
BR (1) BR9304856A (enrdf_load_stackoverflow)
CZ (1) CZ254293A3 (enrdf_load_stackoverflow)
DE (1) DE59309975D1 (enrdf_load_stackoverflow)
TR (1) TR27428A (enrdf_load_stackoverflow)
TW (1) TW268967B (enrdf_load_stackoverflow)

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DE4405358A1 (de) * 1994-02-19 1995-08-24 Hoechst Ag Reaktivfarbstoffmischungen
DE4414320A1 (de) * 1994-04-25 1995-10-26 Hoechst Ag Schwarze Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial
DE19511688C2 (de) * 1995-03-30 1999-07-22 Dystar Textilfarben Gmbh & Co Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial
US5611821A (en) * 1995-09-16 1997-03-18 Everlight Usa, Inc. Black reactive dye composition
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US5989298A (en) * 1997-04-07 1999-11-23 Ciba Speciality Chemicals Corporation Mixtures of reactive dyes and their use
CH692582A5 (de) * 1997-09-26 2002-08-15 Bezema Ag Wasserlösliche Reaktivfarbstoffmischungen und ihre Verwendung zum Färben.
US5931974A (en) * 1998-07-28 1999-08-03 Dystar Textilfarben Gmbh & Co. Deep black dye mixtures of fiber-reactive azo dyes and use thereof for dyeing hydroxy- and/or carboxamido-containing fiber material
US6106580A (en) * 1998-08-27 2000-08-22 Dystar Textilfarben Gmbh & Co. Deutschland Kg Black dye mixtures of fiber-reactive azo dyes and use thereof for dyeing hydroxy--and/or carboxamido-containing fiber material
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US6171349B1 (en) * 1999-01-20 2001-01-09 Everlight Usa, Inc. Reactive dye composition
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US6086639A (en) * 1999-03-09 2000-07-11 Dystar Textilfarben Gmbh & Co. Deutschland Kg Black dye mixtures of fiber-reactive azo dyes and use thereof for dyeing hydroxy- and/or carboxamido-containing fiber material
US6036732A (en) * 1999-04-30 2000-03-14 Dystar Textilfarben Gmbh & Co. Deuschland Kg Black dye mixtures of fiber-reactive azo dyes, methods for their preparation and use thereof for dyeing hydroxy-and/or carboxamido-cont
EP1162211B2 (en) * 1999-06-17 2011-08-24 Mitsui Chemicals, Inc. Ethylene (co)polymers and uses thereof
JP2003503575A (ja) * 1999-06-24 2003-01-28 ダイスター・テクステイルファルベン・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・ドイッチュラント・コマンデイトゲゼルシャフト 反応性染料混合物
US6464734B1 (en) 2000-03-13 2002-10-15 Dystar Textilfarben Gmbh & Co. Deutschland Kg Deep black dye mixtures of fiber-reactive azo dyes
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BR0112766A (pt) 2000-07-25 2003-06-24 Dystar Textilfarben Gmbh & Co Misturas de corante de corantes azo reativos à fibra e seu uso para tingimento de material contendo grupos hidróxi e/ou carboxamido
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KR100368987B1 (ko) * 2000-11-20 2003-01-24 이화산업 주식회사 반응성 흑색 염료 조성물
US6712863B2 (en) 2000-12-11 2004-03-30 Dystar Textilfarben Gmbh & Co. Deutschland Kg Black dye mixtures of fiber-reactive azo dyes, methods for their preparation and use thereof for dyeing hydroxy-and/or carboxamido-containing fiber material
US6623534B2 (en) 2000-12-29 2003-09-23 Dystar Textilfarben Gmbh & Co. Deutschland Kg Black dye mixtures of fiber-reactive azo dyes, methods for their preparation and use thereof for dyeing hydroxy-and/or carboxamido-containing fiber material
KR100391051B1 (ko) * 2001-03-06 2003-07-12 세일화학공업주식회사 신규의 반응성 오렌지 염료
CN1204203C (zh) * 2001-03-29 2005-06-01 大光化学工业株式会社 不对称的偶氮基金属络合染料及其制备方法,含该染料的酸性黑色染料组合物
KR20040010675A (ko) 2001-06-01 2004-01-31 다이스타 텍스틸파르벤 게엠베하 운트 컴파니 도이칠란트 카게 섬유 반응성 아조 염료의 흑색 염료 혼합물, 및하이드록시- 및/또는 카복스아미도 기를 함유하는 물질을염색하기 위한 이들의 용도
KR100427549B1 (ko) * 2002-02-19 2004-04-28 이화산업 주식회사 반응성 흑색 염료조성물
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JPH06263997A (ja) 1994-09-20
US5445654A (en) 1995-08-29
TR27428A (tr) 1995-04-21
EP0600322A2 (de) 1994-06-08
DE59309975D1 (de) 2000-04-20
CZ254293A3 (en) 1994-06-15
KR100293392B1 (ko) 2001-11-22
BR9304856A (pt) 1994-05-31
CN1099052A (zh) 1995-02-22
TW268967B (enrdf_load_stackoverflow) 1996-01-21
EP0600322A3 (de) 1995-02-15

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